Upcoming Events
Embrace the allure of our Eastern Shore haven, where each passing season ushers in its own tapestry of charm and adventure! As we peer into the unfolding year, we're excited to present exciting happenings and unforgettable moments. Whether you're drawn to the vibrant hues of spring's awakening, the spirited festivities of summer's peak, the rustic warmth of autumn's embrace, or the magical enchantment of winter's frost, there's an experience tailored to enchant every soul. Navigate below to find the ideal time to plan your stay.
Fall
Chesapeake Film Festival
The prestigious Chesapeake Film Festival returns to Easton, Maryland from September 27th to September 29th, 2024! Immerse yourself in the magic of cinema with a captivating lineup of acclaimed films, thought - provoking documentaries, and engaging discussions with industry experts.
Fall Into St. Michaels
Fall into the enchantment of St. Michaels during the third weekend in October! Experience the charm of our scenic town as it comes alive with scarecrow contests, pumpkin pie eating competitions, and pumpkin carving festivities scattered throughout. Immerse yourself in the vibrant spirit of the season as you wander the streets adorned with whimsical creations.
Oyster Fest
Get ready to indulge in the flavors of the Chesapeake Bay's favorite fall festival! Join us for Chesapeake Bay Maritime Museum’s Oyster Fest on Saturday, October 26th for a day filled with live music, exciting retriever demonstrations, and of course, mouthwatering oysters and more. Sip on local brews, slurp down freshly shucked oysters, and savor the taste of autumn by the bay. It's an event you won't want to miss!
Waterfowl Festival
Experience the charm of the Eastern Shore at Easton's Waterfowl Festival, taking place from November 8th to 10th, 2024! Delight in a weekend filled with exquisite art collections, culinary delights, and the authentic ambiance of the Chesapeake Bay. Immerse yourself in the rich tradition of waterfowl calling and witness captivating live demonstrations. Don't miss this true Eastern Shore classic, where art, culture, and nature converge for an unforgettable celebration!
Eastern Shore Sea Glass and Coastal Arts Festival
The Holiday Edition of the Eastern Shore Sea Glass and Coastal Arts Festival will take place on Saturday, November 23, 2024, at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. Since 2010, this beloved tradition has showcased a diverse array of artisans and craftspeople from near and far. Attendees can explore and purchase unique coastal and sea glass-themed jewelry, home décor, art, and more.
Lighting of the Lane
Join us November 29th for the enchanting Lighting of the Lane, marking the start of the holiday season. Enjoy delectable lite bites, warming beverages, and the possibility of snowflakes. Keep an eye out for a special visit from the man with the white beard! Celebrate the joy and wonder of the holidays as we come together for this magical moment.
Winter
Midnight Madness
Step into the magic of Midnight Madness the first weekend of December in St. Michaels. Our charming shops extend their hours, welcoming you with festive refreshments, delectable snacks, and exclusive sales. Every purchase at participating businesses brings you closer to winning delightful gift baskets, adding to the joy of the season.
Christmas in St. Michaels
Experience the magic of Christmas in St. Michaels from December 13th to 15th! Join us for a weekend filled with joyous celebrations as our picturesque town comes alive with holiday spirit. Don't miss the enchanting Talbot Street Christmas Parade and the dazzling Lighted Boat Parade, where the waterfront sparkles with festive cheer. Throughout the town, discover a plethora of merry festivities to delight in with loved ones amidst the festive atmosphere of Christmas in St. Michaels.
Spring 2025
Easter
Hop into Perry Cabin this Easter for a brunch celebration like no other! Join us for a delightful feast with Easter egg hunts alongside the beloved Easter Bunny. Gather your family and friends for a day of joy, delicious food, and cherished memories. More details coming soon!
Eastern Shore Sea Glass and Coastal Arts Festival
Save the date for the upcoming Eastern Shore Sea Glass and Coastal Arts Festival, taking place on Saturday, April 12th and Sunday, April 13th at the Chesapeake Bay Maritime Museum in St. Michaels, Maryland. This Spring Edition promises an extraordinary showcase of coastal craftsmanship, with over 90 exhibitors presenting a diverse collection of jewelry, home décor, art, and more.
Mother's Day
For Mother's Day, celebrate the amazing women who deserve to be pampered! Show your love by gifting them an unforgettable experience at Inn at Perry Cabin, where every moment is wrapped in luxury.
Summer 2025
CBMM Antique & Classic Boat Festival and Coastal Arts Fair
Plan ahead for the 37th Antique & Classic Boat Festival at the Chesapeake Bay Maritime Museum! Enhance your experience with a stay at Inn at Perry Cabin for the ultimate Chesapeake retreat. Dates and more information coming soon. In the meantime, check out last year’s festival here for a glimpse of the excitement to come!
Independence Day
Join us for Fourth of July and enjoy front row seats to the St. Michaels' stunning fireworks display on Saturday, July 7th.
Plein Air Easton
Plein Air Easton, celebrating its 21st year July 11 - 20 2024, is the largest juried plein air painting competition in the U.S and a perfect excuse to plan a visit. Hosted by the Avalon Foundation in Easton, Maryland, each July, it draws talented artists from around the world.
